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Synthesis 2014; 46(23): 3273-3282
DOI: 10.1055/s-0034-1379008
DOI: 10.1055/s-0034-1379008
paper
ortho-Ketimines of 1,8-Bis(dimethylamino)naphthalene: Synthesis, Hydrolytic Stability and Transfer of Basicity from Proton Sponge Moiety to the Imino Function
Further Information
Publication History
Received: 25 June 2014
Accepted after revision: 31 July 2014
Publication Date:
26 August 2014 (online)
Abstract
A series of 2-ketimines and 2,7-diketimines of 1,8-bis(dimethylamino)naphthalene (proton sponge, DMAN) have been obtained and converted into the corresponding ketones via acidic hydrolysis. Investigation of structural and spectral properties of DMAN-based imines led to the conclusion that their unusual hydrolytic stability results from a combination of different factors the most important of which is a strong electron-donor effect of peri-dimethylamino groups.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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